It wasn’t so simple for me; I lied awake for hours that night, thinking about what had occurred, how we arrived on this road, and how far could it take us.
Could I as an Aunt travel down this road? And more important, did I want to?
The next morning I woke up around 10, not getting much sleep the night before.
I looked to my side at Tyler, he was still fast asleep.
I got up and had a light snack before starting on breakfast for him. I started my shift at 3 that day; I tried thinking of something to do to kill time until then.
I made breakfast and decided to treat Tyler to breakfast in bed. I carried the tray of food into his room. I slipped my robe loose, once again exposing deep cleavage
“Tyler sweetheart get up, I have a surprise for you.”
He groggily opened his eyes.
I bent over in front him to put the tray in front of him; also to give him a clear view of my cleavage.
His eyes popped wide open, what a site to awaken to!
I held the tray right below my chest; waiting for him to sit up. I put the tray in front of him before finally prying his eyes off my chest by turning around.
“Ty eat fast, were going to go clothes shopping today before my shift, so get ready!”
“Shopping, what are we going to buy?”
“We can look around for stuff. You know I’ve always liked your taste in clothing, I was hoping you could help me out?”
“Yea sure Aunt Carly I’d love to!” he exclaimed
“Alright we’re leaving soon so get your but ready fast!”
I replied as I walked out.
I quickly took a shower and came out dressed in a thigh high skirt and white blouse.
To my surprise he was waiting for me; fully dressed and ready to go.
We walked to the car and soon started off to the mall. I couldn’t help but notice that Tyler had his eyes on my legs the whole trip; scanning them up and down.
I smooched down a little bit on my seat; causing my skirt to hike up; exposing some thigh. This grabbed his attention even more.
I turned to him at a red light.
“So Ty, any ladies in your life at the moment?” I giggled
He pried his eyes off my legs to meet my eyes
“Not really auntie, I mean girls are nice to me a lot but I get really nervous around them.”
“Oh don’t worry Ty that’s natural, we all go through awkward phases around your age, you will get by it, and by the looks of it the girls will be flocking over you soon.” I smiled
“Ha-ha thanks.” He smiled “There are a few girls from school I like, I just hope they like me back.”
“Well just don’t pull their hair or call them names, be nice to them and you’ll be ahead of most boys your age.”
“Yea thanks for the advice Auntie.”
“No problem”
The light turned green
I continued
“Just curious, what do you really like about those girls in your school?”
He got kind of nervous
“Um I don’t know.” He laughed “their personalities.”
“Yea right!” I laughed
“Ok you got me” he confessed “their looks.”
“What specifically about their looks if you don’t mind me asking?”
“Well um, well there is this girl named Breanne, and she is really pretty but what sets her apart from the other girls is her…arm boobs.” He said shyly
“Ha-ha yup those big ole boobs do tend to attract the boys, what else would you like in a girl?”
“Um well, she has to be skinny and in shape. I like them kind of tall, with nice legs and a round you know…butt.”
“Well well, with those expectations I look forward to meeting your future wife someday!” I laughed
He laughed back
we pulled into the mall parking lot and made our way in.
We looked around, I got some jeans for Tyler and he helped me pick out some blouses.
It was then when an idea hit me
“Hmm there is just one more thing I need. Bras, you can help me pick some out but it might be kind of boring so you can wait in the car if you want.”
He shook his head fast
“No Auntie I’ll help you pick some out.” He said; trying to keep his voice calm.
“Well alright, you’ve been so helpful so far it would only make sense if I brought you along for this too!”
Soon we entered Macy’s where I regularly bought my underwear from.
Tyler followed intently as I walked into the women’s underwear section. Tyler was visibly eager.
“So what arm breast size are you Auntie”
“30DD.” I responded “Do you know how bra sizes work Ty.”
He shook his head
“Well, the number in front the diameter of my under cage, the area right below my breasts, a 30 means I have a relatively slim under cage. The letter is the cup size of my actual breasts. And as you probably know a DD cup means I have relatively large breasts.” I explained
“Oh thanks for clarifying Auntie, I’ll look for the perfect one.” He winked as he scampered off into the different aisles.
He came back with an assortment of bras, all different colors and styles.
“I like all of these!” he exclaimed as he piled them into my arms
“hmm, I definitely don’t need all of these, I guess I’ll just try them on and we can decide which ones to keep. Follow me.”
This particular Macy’s had completely separate fitting rooms for the underwear. Luckily it wasn’t particularly bus and I was the only woman trying on bra’s at the moment. I told Ty to sneak in and head around the corner.
Its not like it wasn’t allowed for boys to be in there but a grown woman modeling bras for a young boy would definitely raise some eyebrows.
I followed in when the coast was clear, I entered the dressing room across from the bench Tyler was sitting at. I took in the pile of bras, Tyler waited intently.
I closed the door and took off my blouse and conservative bra that I had on. The first bra I tried on was a black lace bra with floral imprints.
It cupped my breasts beautifully; very comfortable.
I stepped out of the room. Tyler’s eyes lit up. I pushed my chest up and down, giving him a good idea of how it encased my breasts.
“What do you think?” I said while pushing my breasts up with my hands.
“Wow it looks great Auntie, I like it, but it looks a little plain, let’s try on one of the more unique ones.”
“Hmm, alright.”
As I walked back I unhooked the bra and tossed it to Tyler to hold as I covered my boobs with my arm.
“I’ll be out in a second.”
I looked through the pile for one that might impress Tyler a little more. I pulled out a slinky silk white bra. I strapped it on.
Right away I felt the tension on my breasts as pulled my breasts high on my chest. It might have been a little too small, but it could pass.
I inspected myself in the mirror. It did look really sexy. The cups were a little lower cut; exposing some more cleavage then the other one.
I walked out.
“Wow auntie you look great!” he exclaimed, barely able to contain himself “the way the white fabric contrasts with you golden tan skin is so nice!”
I smiled as I bounced my chest up and down; resulting in my breasts almost popping out.
“This one’s a keeper.” He insisted
“I’m glad you like it.” I smiled
I slid it off; once again covering my breasts with my hand. I handed it to him. Right away he started feeling the fabric his aunt’s breasts were in just seconds ago. I walked back into the fitting room. I looked for something that would really wow him.
I picked out a small pink bra. I looked at the label. It seemed Tyler had accidentally grabbed a 30D instead of a 30DD. The model was designed to be a tight fit anyways, to add to that it was a size too small!
I had to use some force just to get the hooks on.
It was so tight it hurt, but the way it made my breasts look was worth it. Naturally it pushed them up, but the fabric was so thin and tight that it indented my breast flesh, making the surrounding flesh bulge out slightly.
The cups were so small that it just barely came up to the upper edge of my nipples.
My edges of my darkish nipples were visible and the shape of them could easily be seen through the thin pink fabric.
I walked out, Tyler’s eyes popped out and his jaws dropped.
He lost control over his words
“Wow Auntie, your breasts look incredible!” he exclaimed “They look so sexy in that little pink bra; they look like they can pop out any second.”
“Wouldn’t you like that?”
“Oh of course I would Auntie, please by this Bra.” He was practically begging
“You know how much I respect your taste Ty, if you like it then I pretty much have to buy it.” I laughed
I flaunted my breasts before him for a little while before I noticed the time, damn we had to get going!
“Alright Ty, I start work soon hun.” I took off the bra once again covering my breasts with my arm and handed it to him.
I changed back to my clothes. We walked out.
We drove home; I walked inside quickly to get ready for work.
I looked at the pink bra lying on the bed and thought to myself I could really get some big tips wearing this thing.
I put it on; picking out a matching pink thong. I put on a sweater and jeans as I usually did to mask my line of work.
I packed my bag and yelled
“Tyler let me show you something.”
He came upstairs.
I lifted my sweater up, he gleamed.
“You’re wearing it!”
“Hell yeah I am! My darling nephew picked it out.”
He smiled
“Too bad no one will be able to see it at the office, a bra like that needs to be seen.”
I thought about what he said
“I agree.” I said
I kissed him goodbye as I started off for the club.
Could I as an Aunt travel down this road? And more important, did I want to?
The next morning I woke up around 10, not getting much sleep the night before.
I looked to my side at Tyler, he was still fast asleep.
I got up and had a light snack before starting on breakfast for him. I started my shift at 3 that day; I tried thinking of something to do to kill time until then.
I made breakfast and decided to treat Tyler to breakfast in bed. I carried the tray of food into his room. I slipped my robe loose, once again exposing deep cleavage
“Tyler sweetheart get up, I have a surprise for you.”
He groggily opened his eyes.
I bent over in front him to put the tray in front of him; also to give him a clear view of my cleavage.
His eyes popped wide open, what a site to awaken to!
I held the tray right below my chest; waiting for him to sit up. I put the tray in front of him before finally prying his eyes off my chest by turning around.
“Ty eat fast, were going to go clothes shopping today before my shift, so get ready!”
“Shopping, what are we going to buy?”
“We can look around for stuff. You know I’ve always liked your taste in clothing, I was hoping you could help me out?”
“Yea sure Aunt Carly I’d love to!” he exclaimed
“Alright we’re leaving soon so get your but ready fast!”
I replied as I walked out.
I quickly took a shower and came out dressed in a thigh high skirt and white blouse.
To my surprise he was waiting for me; fully dressed and ready to go.
We walked to the car and soon started off to the mall. I couldn’t help but notice that Tyler had his eyes on my legs the whole trip; scanning them up and down.
I smooched down a little bit on my seat; causing my skirt to hike up; exposing some thigh. This grabbed his attention even more.
I turned to him at a red light.
“So Ty, any ladies in your life at the moment?” I giggled
He pried his eyes off my legs to meet my eyes
“Not really auntie, I mean girls are nice to me a lot but I get really nervous around them.”
“Oh don’t worry Ty that’s natural, we all go through awkward phases around your age, you will get by it, and by the looks of it the girls will be flocking over you soon.” I smiled
“Ha-ha thanks.” He smiled “There are a few girls from school I like, I just hope they like me back.”
“Well just don’t pull their hair or call them names, be nice to them and you’ll be ahead of most boys your age.”
“Yea thanks for the advice Auntie.”
“No problem”
The light turned green
I continued
“Just curious, what do you really like about those girls in your school?”
He got kind of nervous
“Um I don’t know.” He laughed “their personalities.”
“Yea right!” I laughed
“Ok you got me” he confessed “their looks.”
“What specifically about their looks if you don’t mind me asking?”
“Well um, well there is this girl named Breanne, and she is really pretty but what sets her apart from the other girls is her…arm boobs.” He said shyly
“Ha-ha yup those big ole boobs do tend to attract the boys, what else would you like in a girl?”
“Um well, she has to be skinny and in shape. I like them kind of tall, with nice legs and a round you know…butt.”
“Well well, with those expectations I look forward to meeting your future wife someday!” I laughed
He laughed back
we pulled into the mall parking lot and made our way in.
We looked around, I got some jeans for Tyler and he helped me pick out some blouses.
It was then when an idea hit me
“Hmm there is just one more thing I need. Bras, you can help me pick some out but it might be kind of boring so you can wait in the car if you want.”
He shook his head fast
“No Auntie I’ll help you pick some out.” He said; trying to keep his voice calm.
“Well alright, you’ve been so helpful so far it would only make sense if I brought you along for this too!”
Soon we entered Macy’s where I regularly bought my underwear from.
Tyler followed intently as I walked into the women’s underwear section. Tyler was visibly eager.
“So what arm breast size are you Auntie”
“30DD.” I responded “Do you know how bra sizes work Ty.”
He shook his head
“Well, the number in front the diameter of my under cage, the area right below my breasts, a 30 means I have a relatively slim under cage. The letter is the cup size of my actual breasts. And as you probably know a DD cup means I have relatively large breasts.” I explained
“Oh thanks for clarifying Auntie, I’ll look for the perfect one.” He winked as he scampered off into the different aisles.
He came back with an assortment of bras, all different colors and styles.
“I like all of these!” he exclaimed as he piled them into my arms
“hmm, I definitely don’t need all of these, I guess I’ll just try them on and we can decide which ones to keep. Follow me.”
This particular Macy’s had completely separate fitting rooms for the underwear. Luckily it wasn’t particularly bus and I was the only woman trying on bra’s at the moment. I told Ty to sneak in and head around the corner.
Its not like it wasn’t allowed for boys to be in there but a grown woman modeling bras for a young boy would definitely raise some eyebrows.
I followed in when the coast was clear, I entered the dressing room across from the bench Tyler was sitting at. I took in the pile of bras, Tyler waited intently.
I closed the door and took off my blouse and conservative bra that I had on. The first bra I tried on was a black lace bra with floral imprints.
It cupped my breasts beautifully; very comfortable.
I stepped out of the room. Tyler’s eyes lit up. I pushed my chest up and down, giving him a good idea of how it encased my breasts.
“What do you think?” I said while pushing my breasts up with my hands.
“Wow it looks great Auntie, I like it, but it looks a little plain, let’s try on one of the more unique ones.”
“Hmm, alright.”
As I walked back I unhooked the bra and tossed it to Tyler to hold as I covered my boobs with my arm.
“I’ll be out in a second.”
I looked through the pile for one that might impress Tyler a little more. I pulled out a slinky silk white bra. I strapped it on.
Right away I felt the tension on my breasts as pulled my breasts high on my chest. It might have been a little too small, but it could pass.
I inspected myself in the mirror. It did look really sexy. The cups were a little lower cut; exposing some more cleavage then the other one.
I walked out.
“Wow auntie you look great!” he exclaimed, barely able to contain himself “the way the white fabric contrasts with you golden tan skin is so nice!”
I smiled as I bounced my chest up and down; resulting in my breasts almost popping out.
“This one’s a keeper.” He insisted
“I’m glad you like it.” I smiled
I slid it off; once again covering my breasts with my hand. I handed it to him. Right away he started feeling the fabric his aunt’s breasts were in just seconds ago. I walked back into the fitting room. I looked for something that would really wow him.
I picked out a small pink bra. I looked at the label. It seemed Tyler had accidentally grabbed a 30D instead of a 30DD. The model was designed to be a tight fit anyways, to add to that it was a size too small!
I had to use some force just to get the hooks on.
It was so tight it hurt, but the way it made my breasts look was worth it. Naturally it pushed them up, but the fabric was so thin and tight that it indented my breast flesh, making the surrounding flesh bulge out slightly.
The cups were so small that it just barely came up to the upper edge of my nipples.
My edges of my darkish nipples were visible and the shape of them could easily be seen through the thin pink fabric.
I walked out, Tyler’s eyes popped out and his jaws dropped.
He lost control over his words
“Wow Auntie, your breasts look incredible!” he exclaimed “They look so sexy in that little pink bra; they look like they can pop out any second.”
“Wouldn’t you like that?”
“Oh of course I would Auntie, please by this Bra.” He was practically begging
“You know how much I respect your taste Ty, if you like it then I pretty much have to buy it.” I laughed
I flaunted my breasts before him for a little while before I noticed the time, damn we had to get going!
“Alright Ty, I start work soon hun.” I took off the bra once again covering my breasts with my arm and handed it to him.
I changed back to my clothes. We walked out.
We drove home; I walked inside quickly to get ready for work.
I looked at the pink bra lying on the bed and thought to myself I could really get some big tips wearing this thing.
I put it on; picking out a matching pink thong. I put on a sweater and jeans as I usually did to mask my line of work.
I packed my bag and yelled
“Tyler let me show you something.”
He came upstairs.
I lifted my sweater up, he gleamed.
“You’re wearing it!”
“Hell yeah I am! My darling nephew picked it out.”
He smiled
“Too bad no one will be able to see it at the office, a bra like that needs to be seen.”
I thought about what he said
“I agree.” I said
I kissed him goodbye as I started off for the club.